Iodine → 3-Fluoro-4-iodopyridine-2-carbonitrile

HRID 1374161Notes

Reaction equation

HRID 1374161 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][N:12]=1)#[N:10].[I:18]I>C1COCC1>[F:17][C:16]1[C:11]([C:9]#[N:10])=[N:12][CH:13]=[CH:14][C:15]=1[I:18]

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 70604082-Cyano-3-fluoropyridine

Product 1

HCID 210758673-Fluoro-4-iodopyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of LDA (40.9 mmol, prepared from 11.4 mL of diisopropyl amine and 16.4 mL of 2.5 M n-butyl lithium in hexanes) in 200 mL THF at −78° C. was treated with 2-cyano-3-fluoropyridine (5.0 g, 40.9 mmol) in 50 mL of THF drop-wise. After 10 minutes a solution of iodine (10.4 g, 40.9 mmol) in 10 mL of TBF was added. After 30 minutes the reaction was quenched with 40 mL of water followed by workup with aqueous sodium thiosulfate. The mixture was diluted with ether, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 0–20% ethyl acetate in hexanes to provide 3-fluoro-4-iodopyridine-2-carbonitrile that gave proton NMR spectra consistent with theory.

Workup

  1. customAfter 30 minutes the reaction was quenched with 40 mL of water
  2. additionThe mixture was diluted with ether
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. washeluted with 0–20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5fe83d1dd5fb4aaa9c4829003570bb04
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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